Thomas studied his reflection in the bathroom mirror critically. He looked down as his erection continued to rage despite his attempts to make it disappear. His embarrassment when his stepmother noticed it was palpable.
Fuck! I can't believe I got a visible erection in front of my stepmother. His Speedos could barely contain the large sausage seeking escape. He rolled the waist down and exposed his thick cock. It swung obscenely from his body and pointed straight out from his groin. This is only day one and I've completely embarrassed myself. But then he realized his stepmother did not act bothered by what she saw when he was leaning over her to rub in sunblock.
Instead, she made light of it and even seemed impressed. As much as he wanted to stroke himself to a climax, he didn't want to draw more attention to it. Instead, he peeled off his tight bathing suit and pulled on a pair of loose shorts in an attempt to hide his excitement. His shorts, however, continued to bulge in front. He flushed the toilet even though he hadn't used it and joined Janet in the living room. She sat in a cushioned wicker chair sipping from a wine glass. Another glass sat on the coffee table in front of the couch.
"I see you've changed. Nice to get out of those wet Speedos, huh? I should do the same. This bikini is tighter than it used to be. It must have shrunk." She cupped her huge breasts and giggled.
"Janet, I'm so embarrassed about what just happened. You probably think I'm weird, don't you?"
"No worries, Thomas. On the contrary--I think you are a normal nineteen-year-old. I'm flattered that whatever got you excited happened around me. I don't get to see anything like that anymore. Pardon me for saying this, but based on what I saw a while ago, you will make someone happy with that weapon someday. No need to hide your feelings. I understand how hormones work. I only wish I knew a way to ease your pain. Maybe you'll meet some nice young girls while you are here, and...well...you know. Just make sure you use protection if the opportunity arises—no pun intended.” She giggled at her joke.
Thomas sipped his wine but looked uncomfortable. His stepmother’s frank talk was a new step in their relationship.
“Listen, Honey, we’re going to be here for a while and we might as well be honest with one another. Your father and I had a very active sex life and I do miss that, but now I have to keep those urges in check. If I were a younger version, I would probably be all over a hunk like you. Unfortunately, life has dealt both of us a shitty hand, but those are the cards we have to play with. So, we might as well make the best of our time here. I hope I’m not embarrassing you with my straight talk. I want both of us to have a wonderful time while we’re here. And if you have urges that are normal for a guy your age, please don’t let me stop you. I want this to be a wonderful vacation for both of us--especially you. You just lost your father and you deserve whatever goodness can come out of this. So come over here and hug me. I need reassurance also.”
Janet held her arms open, and Thomas got up and walked to her.
"And by the way, Thomas, there is no need to try and hide your erections. I’ve seen plenty of them in my day. In fact, I kind of like seeing them. As I said, it’s just a normal reaction to environmental conditions. I was just a little surprised when I sat up and it hit me in the face! I realize men your age go gaga over a set of boobs like mine. I am used to my perky nipples preventing men from knowing what color my eyes are. It’s a pretty common reaction. So, no worries, Thomas. Go ahead and stare at me if you feel the need. I’m flattered. I like having a good looking man admire me."
Janet stood, threw back her shoulders, and embraced her stepson. She squeezed him tightly, pressing him into her huge breasts as she felt that familiar lump forming in his groin again. At only 5'5" she had to stand on her tip toes to get her face close to his. Thomas bent down and kissed her forehead. She smiled and kissed him on the cheek. And then she pulled him even closer and whispered in his ear as if someone might overhear her.
"I know Glen's death has brought us closer together. Your dad was wonderful, and I loved him with all my heart. Before he died he asked me to make sure you were happy, and I swore that I would. Not that you need an old gal like me to boost your spirits, but I figured this trip would seal the deal. I want you to be open and honest with me. I feel like we are more than mother and stepson at this point. You remind me so much of Glen in many ways: your looks, your habits, even the way you laugh. And yes, your dad loved my boobs, too. So if I show a little skin under the Caribbean sun, don't be alarmed. I'm just an old lady who likes flaunting it a bit."
"Janet, I appreciate everything you are saying. I couldn't have asked for a better travel companion. And I noticed that men and women in the airports seemed to look at us as if we were a couple. One guy even remarked to me in the bathroom how hot my girlfriend was. I didn't bother to tell him you were my mother."
Oh, Honey. That's so nice to hear. Thank you. I needed that. I still feel young, but I know it's only a matter of time and I'll be strapping a belt around these puppies instead of a bra. But they're holding up pretty well for my age, don't you think? Your father and I were always pretty conservative around you and others, but he had a playfully nasty streak in the bedroom. Not that you need to hear about that. I miss him terribly, but you're helping me just by being here."
Janet squeezed him again. "Hey! Let's snuggle on the couch and watch the sunset. This is so beautiful."
She led him back to the couch, and they cuddled as they sipped their wine. He threw his arm around her and they stayed this way, talking and snuggling, giggling and teasing. Soon the bottle of wine was gone and the alcohol combined with the heat was working its magic. They both felt a little giddy and sleepy.
As the sun slowly dipped toward the ocean and the colors faded in the dusk, they sat silently and took it all in. Janet's eyes closed and she became quiet. Soon she was quietly snoring and Thomas realized she had fallen asleep in his arms. Her head had gradually slid from his chest to his stomach and now she had slipped ever farther so that her cheek was resting on his lap with one arm draped across his thighs. Her huge breasts pressed into his legs and part of one large nipple peeked out of her top. As if on cue, his cock began to grow.
As he watched his stepmom softly dozing in the diminishing light, he imagined her having sex with his father. He looked at her full lips and pictured her with his father's cock in her mouth while he fondled those firm breasts. And then the image changed, and it was him kneading that pliant flesh as she slowly inhaled his cock, her lips stretched and saliva dripping from her mouth as he had seen countless times on porn sites. It seemed so real.
Jesus, Thomas. Think of something else...anything else. But then he saw in horror that his erection was now sticking out the leg of his nylon shorts. The plum-sized helmet was visible, even in the fading light.
Fuck! What if she wakes up? He tried to carefully adjust things so that his cock was hidden again, but he didn't want to wake her. in the process. She moaned and moved her head slightly which only made it worse. Now her lips were almost touching his large cock head. And then he watched in shock as her lips brushed against the head and opened slightly in response, allowing the tip of his glans to slip between them.